Abstract
Novel fluorine substituted α-amino phosphonic acids containing 1,2,4-triazin- 5-one (6a-f) have been obtained from fluoroacylation of 6-(2′-amino-5′-nitrophenyl)-3-thioxo-1,2,4-triazin-5(4H)-one (1) followed by ammonilysis to give the corresponding 3-amino-derivative 3. Condensation of compound 3 with nitro/halogenated aromatic aldehydes yielded the Schiff bases 4. The simple addition of diethyl phosphonate to compound 4 produced the α-amino phosphonates 5. Acidic hydrolysis of compound 5 produced the fluorine substituted α-amino acids derivatives 6. Structures of the new compounds have been established with the help of elemental analysis and spectral measurements. Also, the products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems.
Highlights
IntroductionΑ-amino phosphonic acids and α-amino phosphonates have a vital importance of research chemists [1] [2] [3], which is due to these family of compounds display, enzymatic inhibitors for HIV protease antagonists [4] and collagenase inhibitors [5]
The products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems
Α-amino phosphonic acids and α-amino phosphonates have a vital importance of research chemists [1] [2] [3], which is due to these family of compounds display, enzymatic inhibitors for HIV protease antagonists [4] and collagenase inhibitors [5]
Summary
Α-amino phosphonic acids and α-amino phosphonates have a vital importance of research chemists [1] [2] [3], which is due to these family of compounds display, enzymatic inhibitors for HIV protease antagonists [4] and collagenase inhibitors [5]. They use as anticancer [6], antibacterial [7], antiviral [8] and antioxidant [9] agents. We focused on the reactivity of functional 1,2,4-triazines towards different reagents followed by simple addition of diethyl phosphonate to obtain a novel fluorine substituted α-amino phosphonic acids which considered as α-amino acids analog, in view of antioxidant activity
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